50 Rom-Com Movie Trivia Questions For Hopeless Romantics

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Are you a hopeless romantic with a penchant for happy tears, heart-fluttering moments, and lovey-dovey endings? If that sounds like you to a tee, we’ve crafted a delightful batch of trivia questions just for you and all the rom-coms you’re obsessed with!

Whether you’re a die-hard fan of the classics like When Harry Met Sally... or can’t get enough of the modern-day charm of To All the Boys I’ve Loved Before, this trivia is the perfect way to test your knowledge and relive your favorite cinematic love stories.

So grab your girlfriends/family, snuggle up with your loved one (or your cat, we don’t judge!), and get ready to swoon over our love-infused trivia quiz.


Robert Indiana Love Sculpture - Valentine's Day Trivia

Q: In 50 First Dates, why are Adam Sandler and Drew Barrymore going on so many first dates?

A: She has amnesia and forgets him when she falls asleep, so he resolves to win her over again each new day.

Q: In 2021’s most-talked-about musical, Lin-Manuel Miranda’s ___, follows a young storeowner from Washington Heights and his neighborhood friends as they juggle their heritage, love, and wanting more for themselves outside of the Heights.

A: In the Heights.

Q: Cleopatra Coleman stars as Sara, a novelist struggling with writer’s block who finds much-needed inspiration from Godfrey, a grief-stricken 30something whom she meets one night at an art museum. What movie is this?

A: The Right One.

Q: This movie is about Rafe Spall as Teddy, whose life is suddenly stuck in fast-forward the day after his wedding, and each year of his life starts passing every few minutes. What’s the title of the film?

A: Long Story Short.

Q: In The Princess Bride, what is the name of the main character played by Cary Elwes?

A: Westley.

Q: What 2012 film stars Bradley Cooper and Jennifer Lawrence and involves a dance competition?

A: Silver Linings Playbook.

Q: In “13 Going on 30,” what is the name of the magazine that Jenna Rink works for?

A: Poise.

Q: Which rom-com movie features the famous line, “I’ll have what she’s having”?

A: When Harry Met Sally…

Q: Who plays the male lead in “Pretty Woman” opposite Julia Roberts?

A: Richard Gere.

Q: In “Crazy, Stupid, Love,” who plays the smooth-talking Jacob Palmer?

A: Ryan Gosling.

Q: Which romantic comedy features Tom Hanks and Meg Ryan and involves them falling in love via a radio show?

A: Sleepless in Seattle.

Q: In “Love Actually,” who plays the British Prime Minister?

A: Hugh Grant.

Q: “The Proposal” stars Sandra Bullock and which actor as her assistant turned fake fiancé?

A: Ryan Reynolds.

Q: Which 2003 romantic comedy features an ensemble cast including Keira Knightley, Hugh Grant, and Colin Firth?

A: Love Actually.

Q: In “Bridget Jones’s Diary,” who are the two men vying for Bridget’s affection?

A: Mark Darcy and Daniel Cleaver, portrayed by Colin Firth and Hugh Grant.

Q: In “Clueless,” who is Cher’s stepbrother and eventual love interest?

A: Josh.

Q: Which 2004 movie has a teenage girl wake up to find herself suddenly 30 years old?

A: 13 Going on 30.

Q: Who plays the role of the “financially poor” Annie in “Bridesmaids”?

A: Kristen Wiig.

Q: “How to Lose a Guy in 10 Days” stars which actress opposite Matthew McConaughey?

A: Kate Hudson.

Q: Which movie features a scene where the main character holds up cue cards to express his love silently?

A: Love Actually.

Q: Who plays the title character in “Maid in Manhattan”?

A: Jennifer Lopez.

Q: In “Crazy Rich Asians,” what is the name of the male lead character that everyone in Singapore knows of?

A: Nick Young.

Q: Which movie features the character Elle Woods attending Harvard Law School?

A: Legally Blonde.

Q: In “Notting Hill,” what is the profession of Hugh Grant’s character, William Thacker?

A: Bookshop owner.

Q: Who stars as the lead in the Netflix hit movie “To All the Boys I’ve Loved Before”?

A: Lana Condor.

Q: “Four Weddings and a Funeral” features which actor as the bumbling Charles?

A: Hugh Grant.

Q: In “10 Things I Hate About You,” who plays the character Patrick Verona?

A: Heath Ledger.

Q: Which 2008 film stars Katherine Heigl and James Marsden in a story about a perennial bridesmaid?

A: 27 Dresses.

Q: Who plays the role of Violet in “The Holiday”?

A: Cameron Diaz.

Q: In “Knocked Up,” who is the actor that plays the character Ben Stone?

A: Seth Rogen.

Q: In “Never Been Kissed,” what is Drew Barrymore’s character’s profession?

A: Journalist.

Q: Which romantic comedy features the iconic scene where Meg Ryan fakes an orgasm in a diner?

A: When Harry Met Sally…

Q: Who stars as the lead character in “The Big Sick,” playing a fictionalized version of himself, a stand-up comedian working in Chicago dealing with the weight of his parents’ expectations?

A: Kumail Nanjiani.

Q: In “Moonstruck,” who plays the male lead, Ronny Cammareri?

A: Nicolas Cage.

Q: “As Good as It Gets” features which actor in the role of Melvin Udall?

A: Jack Nicholson.

Q: In “Say Anything…,” what song is playing during the iconic boombox scene?

A: “In Your Eyes” by Peter Gabriel.

Q: Who plays the character of Kat Stratford in “10 Things I Hate About You”?

A: Julia Stiles.

Q: “The 40-Year-Old Virgin” stars Steve Carell as Andy. What is Andy’s hobby?

A: Collecting action figures.

Q: In “Hitch,” who plays the role of Sara Melas, opposite Will Smith?

A: Eva Mendes.

Q: Who plays the lead role in “Trainwreck”?

A: Amy Schumer.

Q: Who plays the male lead in “27 Dresses”?

A: James Marsden.

Q: “Palm Springs” stars Andy Samberg and which actress as the main couple?

A: Cristin Milioti.

Q: Which romantic comedy features a couple falling in love during a worldwide pandemic?

A: The Big Sick.

Q: In “You’ve Got Mail,” what is the name of the bookstore owned by Meg Ryan’s character?

A: The Shop Around the Corner.

Q: “Coming to America” stars Eddie Murphy as a prince from which fictional African country?

A: Zamunda.

Q: “The Holiday” stars which two actresses as the main characters who swap homes?

A: Cameron Diaz and Kate Winslet.

Q: In “Definitely, Maybe,” who plays the character of Will Hayes?

A: Ryan Reynolds.

Q: “Moonstruck” features which actress in the role of Loretta Castorini?

A: Cher.

Q: In “The Wedding Singer,” which actress plays Julia, Adam Sandler’s love interest?

A: Drew Barrymore.

Q: Which movie features a bet where the male lead has to make a woman fall in love with him in 10 days?

A: How to Lose a Guy in 10 Days.

Q: “My Best Friend’s Wedding” stars Julia Roberts. Who plays her best friend, Michael?

A: Dermot Mulroney.

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    Elle Liang

    Elle is a travel blogger and entertainment publisher by day and a trivia fanatic by night. Her favorite hobbies include hiking mountains, traveling anywhere in the world, watching documentaries, playing bingo, and brushing up on world knowledge through games like Trivial Pursuit.

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